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Scopolin

CAT: 0804-HY-N0341-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N0341-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2].
CAS Number
531-44-2
UNSPSC
12352005
Target
Sirtuin
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage; Epigenetics
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/scopolin.html
Purity
99.93
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C1C=CC2=CC(OC)=C(O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)C=C2O1
Molecular Formula
C16H18O9
Molecular Weight
354.31
References & Citations
[1]Siwinska J, et al. Identification of QTLs affecting scopolin and scopoletin biosynthesis in Arabidopsisthaliana. BMC Plant Biol. 2014 Oct 18;14:280. |[2]Yoo A, et al. Scopolin ameliorates high-fat diet induced hepatic steatosis in mice: potential involvement of SIRT1-mediated signaling cascades in the liver. Sci Rep. 2017 May 22;7 (1) :2251.|[3]Rollinger JM, et al. Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. J Med Chem. 2004 Dec 2;47 (25) :6248-54.|[4]Pan R, et al. Scopolin isolated from Erycibe obtusifolia Benth stems suppresses adjuvant-induced rat arthritis by inhibiting inflammation and angiogenesis. Int Immunopharmacol. 2009 Jul;9 (7-8) :859-69. |[5]Lee SH, et al. Scopoletin and scopolin isolated from Artemisia iwayomogi suppress differentiation of osteoclastic macrophage RAW 264.7 cells by scavenging reactive oxygen species. J Nat Prod. 2013 Apr 26;76 (4) :615-20.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
SIRT1

Chemical Information

Scopolin

Scopolin is a member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a beta-D-glucoside, a member of coumarins and a monosaccharide derivative. It is functionally related to a scopoletin.

CAS Number531-44-2
PubChem CID439514
IUPAC Name6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
Molecular FormulaC16H18O9
Molecular Weight354.31
XLogP-1.1
Topological Polar Surface Area135
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Heavy Atom Count25
Formal Charge0
Complexity510
SMILES
COC1=C(C=C2C(=C1)C=CC(=O)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChI
InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
InChIKey
SGTCGCCQZOUMJJ-YMILTQATSA-N
Chemical Structure
2D Structure
2D structure of Scopolin
CAS: 531-44-2
CID: 439514
Formula: C16H18O9
MW: 354.31
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight354.31
XLogP3-1.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Exact Mass354.09508215
Monoisotopic Mass354.09508215
Topological Polar Surface Area135 Ų
Heavy Atom Count25
Formal Charge0
Complexity510
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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